Fungicidal mixture

ABSTRACT

A composition comprising effective amounts of 
     a) a compound of the formula I                    
      or an N-oxide or salt thereof, wherein 
     R 1 , R 2 , R 3  and R 4  are hydrogen, hydroxyl, nitro, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio or haloalkylthio; 
     R 5 , R 6  and R 7  are hydrogen, hydroxyl, cyano, nitro, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, hydroxyalkyl, acyl, aryl or aryloxy, wherein the aryl groups are optionally substituted, and 
     e) a compound of the formula V                    
      wherein 
     R 10  is fluorine or chlorine; 
     R 11  is trifluoromethyl or chlorine, or 
     R 10  and R 11  together are a group —OCF 2 O—, exhibits a synergisitc fungicidal effect.

This is a Divisional Application of application Ser. No. 08/849,126,filed on Jun. 16, 1997, (now U.S. Pat. No. 6,075,030) which is aNational Stage Application under 35 U.S.C. 371, based on InternationalApplication No. PCT/EP 95/04,785, filed Dec. 05, 1995.

The present invention relates to a fungicidal mixture comprising

a) a compound of the formula I

 an N-oxide or a salt thereof, where the radicals are defined asfollows:

R¹,R², R³ and R⁴ independently of one another are: hydrogen, hydroxyl,nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio;

R⁵,R⁶ and R⁷ independently of one another are: hydrogen, hydroxyl,cyano, nitro, halogen, C₁-C₇-alkyl, C₁-C₇-haloalkyl, C₁-C₇-alkoxy,C₁-C₇-haloalkoxy, C₁-C₇-alkylthio, C₁-C₇-haloalkylthio,C₁-C₇-hydroxyalkyl, C₂-C₄-acyl, aryl or aryloxy, it being possible forthe radicals with aryl to have attached to them, in turn, one to threeof the following groups: cyano, nitro, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio andC₁-C₄-haloalkylthio, or

b) a compound of the formula II,

 where the radicals are defined as follows:

R⁸ is phenyl which can have attached to it one to three of the followinggroups: cyano, halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl and C₁-C₄-alkoxy,or

 pyrimidyl which can have attached to it a C₁-C₃-alkyl group and/or aphenoxy group, it being possible for the phenoxy group to have attachedto it, in turn, one to three of the following substituents: cyano,halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl and C₁-C₄-alkoxy;

A is oxygen or oxymethylene (—OCH₂—);

X is CH or N;

Y is oxygen or NR, where R is hydrogen, C₁-C₃-alkyl or C₁-C₃-alkoxy, or

c) a pyrimidine derivative of the formula III

 or a salt thereof where the radical R⁹ is methyl, propyn-1-yl orcyclopropyl, or

d)(2RS,3SR)-1-[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-ylmethyl]-1H-1,2,4-triazole(IV)

 or

e) a compound of the formula V

 in which the radicals are as defined below:

R¹⁰ is fluorine or chlorine;

R¹¹ is trifluoromethyl or chlorine, or

R¹⁰ and R¹¹ together are a group —OCF₂O—,

in a synergistically active amount.

The invention furthermore relates to methods of controlling fungal pestsusing the compounds I and a compound II to V, or synergistic mixturescomprising them, and to the use of the compounds I, or the compounds IIto V, for the preparation of such mixtures.

U.S. Pat. No. 5,240,940 and ACS Sympos. Ser. 443, page 538 to page 552(1991) disclose compounds of the formula I, their fungicidal action andtheir preparation.

The literature (EP-A 253 213, EP-A 382 375, EP-A 398 692, EP-A 400 417)also discloses compounds of the formula II, their preparation and theiraction against fungal pests.

Also known are the pyrimidine derivatives III, their preparation andtheir action against fungal pests [R⁹=methyl: DD-A 151 404 (common name:pyrimethanil); R⁹=1-propynyl: EP-A 224 339 (common name: mepanipyrim);R⁹=cyclopropyl: EP-A 310 550 (common name: cyprodinil)].

EP-A 196 038 discloses (2RS,3SR)-1-[3-(2-chlorophenyl)-2-(4-40fluorophenyl)oxiran-2-ylmethyl]-1-1-1,2,4-triazole (IV) (INN name:epoxiconazole).

EP-A 318 704 (R¹⁰=F, R¹¹=CF₃), -EP-A 206 999 (R¹⁰, R¹¹=—O—CF₂—O—: commonname: fludioxonil) and EP-A 182 738 (R¹⁰, R¹¹=chlorine: common name:fenpiclonil) also disclose the compounds of the general formula V.

With a view to reducing the rates of application and to improving thespectrum of action of the known compounds, it is an object of thepresent invention to provide mixtures which have an improved activityagainst fungal pests while the total amount of active ingredientsapplied is reduced (synergistic mixtures).

We have found that this object is achieved by the mixtures defined atthe outset. Moreover, it has been found that fungal pests can becontrolled more efficiently when the compounds I and the compounds II toV are applied simultaneously, i.e. jointly or separately, or when thecompounds I-and the compounds II to V are applied in succession, thanwhen the compounds I or II to V are used alone.

Relative to the C═X double bond, the compounds of the formula II canexist in the E or the Z configuration (relative to the OCH₃ and CO—YCH₃group). Accordingly, they can be used in the mixture according to theinvention either in the form of the pure isomers or in the form of amixture of E/Z isomers. The mixture of E/Z isomers or the E isomer ispreferably used, the E isomer being particularly preferred in manycases.

Due to the basic character of the ring nitrogen atom or the NH group,the compounds I and III are capable of forming salts with inorganic ororganic acids or with metal ions.

Examples of inorganic acids are hydrohalic acids, such as hydrogenfluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide,sulfuric acid, phosphoric acid and nitric acid.

Suitable organic acids are, for example, formic acid, carbonic acid andalkanoic acids, such as acetic acid, trifluoroacetic acid,trichloroacetic acid and propionic acid, and also glycolic acid,thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid,cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids havingstraight-chain or branched alkyl radicals having 1 to 20 carbon atoms),arylsulfonic acids or aryldisulfonic acids (aromatic radicals such asphenyl and naphthyl which have attached to them one or two sulfonic acidgroups), alkylphosphonic acids (phosphonic acids having straight-chainor branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonicacids or aryldiphosphonic acids (aromatic radicals such as phenyl andnaphthyl which have attached to them one or two phosphoric acidradicals), it being possible for the alkyl or aryl radicals to haveattached to them further substituents, for example p-toluenesulfonicacid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid,2-acetoxybenzoic acid and the like.

Suitable metal ions are, in particular, the ions of the elements of thesecond Main Group, in particular calcium and magnesium, of the third andfourth Main Group, in particular aluminum, tin and lead, and of thefirst to eighth Sub-group, in particular chromium, manganese, iron,cobalt, nickel, copper and zinc. Particularly preferred metal ions arethose of the elements of the Sub-groups of the fourth period. The metalcan exist at the various valency levels which they assume.

Furthermore, the compounds I can be converted in a manner known per seto give the N-oxides (cf. U.S. Pat. No. 5,240,940).

Compounds I and their salts or N-oxides which are preferably used forproviding the fungicidal mixtures according to the invention are thosewhere the radicals are defined as follows:

R¹,R²,R³ and R⁴ independently of one another are hydrogen, halogen,C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkoxy, C₁-C₂-haloalkoxy orC₁-C₂-alkylthio; and

R⁵,R⁶ and R⁷ independently of one another are hydrogen, nitro, cyano,halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or phenyl.

With a view to the applicability as components in the mixture,particularly preferred compounds are the compounds Ia as shown in Table1 below.

TABLE 1 (Ia)

No. R¹ R² R³ R⁴ R⁵ 1 H H Cl H 2-F 2 H H Cl H 2-C(CH₃)₃ 3 H H Cl H 2-CH₃4 H H Cl H 2-OCH₃ 5 H H Cl H 3-F 6 H H Cl H 3-Cl 7 H H Cl H 3-CF₃ 8 H HCl H 3-CN 9 H H Cl H 3-OCH₃ 10 H H Cl H 3-phenyl 11 H H Cl H 4-Cl 12 H HCl H 4-Br 13 H H Cl H 4-CF₃ 14 H H Cl H 4-CH₃ 15 H H Cl H 4-CH(CH₃)₂ 16H H Cl H 4-CN 17 H H Cl H 2-Cl-4-F 18 H H Cl H 2,4-di-Br 19 H H Cl H2,4-di-NO₂ 20 H H Cl H 2-CH₃-4-F 21 H H Cl H 2,6-di-F 22 H H Cl H2,4,6-tri-CH₃ 23 F H H H 4-F 24 Cl H H H 4-F 25 NO₂ H H H 4-F 26 H F H H4-F 27 H Cl H H 4-F 28 H CH₃ H H 4-F 29 H NO₂ H H 4-F 30 H OC₂H₅ H H 4-F31 H H F H 4-F 32 H H Cl H 4-F 33 H H Br H 4-F 34 H H NO₂ H 4-F 35 H HOCF₃ H 4-F 36 H H C₂H₅ H 4-F 37 H H SCF₃ H 4-F 38 H H O—C₂H₅ H 4-F 39 HH H F 4-F 40 H H H Cl 4-F 41 H H H CF₃ 4-F 42 F H F H 4-F 43 O—CH₃ HO—CH₃ H 4-F 44 Cl F H H 4-F 45 Cl Cl H H 4-F 46 Cl CH₃ H H 4-F 47 H Br HCl 4-F 48 H Cl H OH 4-F 49 H O—CH₃ H NO₂ 4-F 50 H F Cl H 4-F 51 H CH₃ ClH 4-F 52 H H Cl Cl 4-F 53 Cl H H Cl 4-F 54 Cl F Cl H 4-F 55 H H Cl CN4-F 56 Cl CH₃ Cl H 4-F 57 Cl Cl Cl H 4-F 58 Cl Cl Cl Cl 4-F 59 H H H Cl2-F-4-Br 60 H H H Cl 2,3-di-CH₃ 61 H H H Cl 2-F-4-Cl 62 H H H Cl2,4-di-Cl-6-F 63 H H H Cl 2,4-di-F 64 H H H Cl 2,4-di-CH₃ 65 H H H Cl2-C₂H₅ 66 H H H Cl 2-CH₃-4-F 67 H H H Cl 3-CH₃-4-Cl 68 H H Cl H H 69 ClH Cl H H 70 H H Cl H 4-C(CH₃)₃

Very particularly preferred compounds are the compounds Ia as shown inTable 2, and the hydrochloride and N-oxide of compound 8 mentionedtherein.

TABLE 2 No. R¹ R² R³ R⁴ R⁵ 1 H H Cl H 2-Cl 2 H H Cl H 2-Br 3 H H Cl H2-CN 4 H H Cl H 2-CF₃ 5 H H Cl H 2-NO₂ 6 H H Cl H 4-F 7 H H Cl H2,4-di-F 8 Cl H Cl H 4-F 9 H H H Cl 2-Cl-4-F 10 CH₃ H CH₃ H 4-F

U.S. Pat. No. 5,240,940 and/or ACS Sympos. Ser. 443, page 538 to page552 (1991) disclose the compounds of the formula Ia mentioned in or inconnection with Tables 1 and 2.

Preferred compounds II for providing the fungicidal mixtures accordingto the invention

are those where the radicals are defined as follows:

R⁸ is phenyl which can have attached to it one to three of the followinggroups: cyano, halogen, C₁-C₂-alkyl, C₁-C₂-haloalkyl and C₁-C₂-alkoxy,or

 pyrimidyl which can have attached to it a C₁-C₂-alkyl group and/or aphenoxy group, it being possible for the phenoxy group, in turn, to haveattached to it one to three of the following substituents: cyano,halogen, C₁-C₂-alkyl, C₁-C₂-haloalkyl and C₁-C₂-alkoxy,

A is oxygen or oxymethylene (—OCH₂—);

X is CH or N; and

Y is oxygen or NR, where R is hydrogen, C₁-C₂-alkyl and C₁-C₂-alkoxy.

Particularly preferred fungicidal mixtures are those which comprisecompounds II where the radicals are defined as follows:

R⁸ is phenyl which can have attached to it one to three of the followinggroups: halogen, methyl, trifluoromethyl and methoxy,

A is oxymethylene (—OCH₂—),

X is CH or N; and

Y is oxygen or NR, where R is hydrogen, methyl and methoxy.

Other particularly preferred fungicidal mixtures are those whichcomprise compounds II where the radicals are defined as follows:

R⁸ is pyrimidyl, in particular pyrimidin-4,6-diyl which can haveattached to it a methyl group and/or a phenoxy group, it being possiblefor the phenoxy group, in turn, to have attached to it one to three ofthe following substituents: cyano, halogen, methyl, trifluoromethyl andmethoxy,

A is oxygen;

X is CH or N; and

Y is oxygen or NR, where R is hydrogen, methyl or methoxy.

Other particularly preferred mixtures are those which comprise acompound of the formula II where R⁸ is 2-methylphenyl or2,5-dimethylphenyl, A is oxymethylene, X is N and Y is oxygen or NH.

In addition, mixtures are preferred which comprise a compound of theformula II where R⁸ is 2-methylphenyl or 2,5-dimethylphenyl, A isoxymethylene, X is N and Y is NH.

Other preferred mixtures are those which comprise a compound of theformula II where R⁸ is 6-(2-cyanophenoxy)pyrimidin-4-yl, A is oxygen, Xis CH and Y is oxygen.

With a view to the applicability as components in the mixture,particularly preferred compounds are the compounds II.A, II.B, II.C,II.D and II.E.

Compounds V.A, V.B and V.C below are preferably used for providing thefungicidal mixtures according to the invention:

Preferably, the pure active ingredients I and II to V are employed forproviding the mixtures, to which further active ingredients againstfungal pests or other pests such as insects, arachnids or nematodes, orelse herbicidal or growth-regulating active ingredients or fertilizersmay be admixed, as required.

The mixtures of the compounds I and II to V, ot the compounds I and IIto V, are applied simultaneously, i.e. jointly or separately or insuccession, and are distinguished by an outstanding activity against abroad spectrum of phytopathogenic fungi, in particular from the classesof the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes.Some of them act systemically and can therefore also be used as leaf-and soil-acting fungicides.

They are particularly important for controlling a large number of fungion a variety of crop plants such as cotton, vegetable species (forexample cucumbers, beans and cucurbits), barley, grass, oats, coffee,maize, fruit plants, rice, rye, soya bean, grapevine, wheat,ornamentals, sugar cane and a variety of seeds.

They are especially suitable for controlling the followingphytopathogenic fungi: Erysiphe graminis (powdery mildew) in cereals,Erysiphe cichoracearum and Sphaerotheca fuliginea in cucurbits,Podosphaera leucotricha in apples, Puccinia species in cereals,Rhizoctonia species in cotton and turf, Ustilago species in cereals andsugar cane, Venturia inaequalis (scab) in apples, Helminthosporiumspecies in cereals, Septoria nodorum in wheat, Botrytis cinera (graymold) in strawberries and grapevines, Cercospora arachidicola ingroindnuts, Pseudocercosporella herpotrichoides in wheat and barley,Pyricularia oryzae in rice, Phytophthora infestans in potatoes andtomatoes, Plasmopara viticola in grapevines, Alternaria species invegetables and fruit, and Fusarium and Verticillium species.

They can furthermore be used in the protection of materials (for examplethe protection of wood), for example against Paecilomyces variotii.

The compounds I and II to V can be applied simultaneously, ie. jointlyor separately, or in succession. If they are applied separately, thesequence has generally no effect on the result.

The compounds I and II to V are usually applied in a ratio by weight of10:1 to 0.1:1, preferably 5:1 to 0.2:1, especially 3:1 to 0.3:1.

Depending on the nature of the desired effect, the rates of applicationof the mixtures according to the invention are 0.01 to 3 kg/ha,preferably 0.1 to 1.5 kg/ha, especially 0.4 to 1.0 kg/ha. The rates ofapplication are 0.01 to 0.5 kg/ha in the case of the compounds I,preferably 0.05 to 0.5 kg/ha, especially 0.05 to 0.2 kg/ha. The rates ofapplication for the compounds II to V are, accordingly, 0.1 to 1.0kg/ha, preferably 0.4 to 1.0 kg/ha, especially 0.4 to 0.8 kg/ha.

In the treatment of seed, rates of application of 0.001 to 50 g of themixture per kg of seed are generally used, preferably 0.01 to 10 g/kg,especially 0.01 to 8 g/kg.

If, in the case of plants, pathogenic fungal pests are to be controlled,the compounds I and II to V or the mixtures of the compounds I and II toV are applied separately or jointly by spraying or dusting the seeds,the plants or the soils before or after sowing the plants, or before orafter plant emergence.

The fungicidal synergistic mixtures according to the invention, or thecompounds I and II to V, can be processed for example in the form ofready-to-spray solutions, powders and suspensions or in the form ofhigh-percentage aqueous, oily or other suspensions, dispersions,emulsions, oil dispersions, pastes, dusts, spreading materials orgranules, and applied by means of spraying, atomizing, dusting,spreading or pouring. The use form depends on the intended use; inany-case, it should guarantee as fine and uniform a distribution of themixture according to the invention as possible.

The formulations are prepared in a manner known per se, for example byadding solvents and/or carriers. Inert additives such as emulsifiers ordispersants are customarily admixed to the formulations.

Suitable surfactants are the alkali metal, alkaline earth metal orammonium salts of aromatic sulfonic acids, for example lignosulfonicacid, phenolsulfonic acid, naphthalenesulfonic acid anddibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- andalkylaryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates,and salts of sulfated hexa-, hepta- and octadecanols or of fatty alcoholglycol ethers, condensates of sulfonated naphthalene and its derivativeswith formaldehyde, condensates of naphthalene or of naphthalenesulfonicacids with phenol and formaldehyde, polyoxyethylene octylphenol ether,ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl polyglycolethers or tributylphenyl polyglycol ether, alkylaryl polyether alcohols,isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylenealkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignin-sulfite waste liquors or methylcellulose.

Powders, spreading materials and dusts can be prepared by mixing orconcomitantly grinding the compounds I to V or the mixture of thecompounds I and II to V together with a solid carrier.

Granules (e.g. coated granules, impregnated granules and homogeneousgranules) are conventionally prepared by binding the active ingredient,or active ingredients, to a solid carrier.

Fillers or solid carriers are, for example, mineral earths such assilica gel, silicic acids, silica gels, silicates, talc, kaolin,limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth,calcium sulfate, magnesium sulfate, magnesium oxide, ground syntheticmaterials, and fertilizers, such as ammonium sulfate, ammoniumphosphate, ammonium nitrate, ureas and products of vegetable origin,such as cereal meal, tree bark meal, wood meal and nutshell meal,cellulose powder or other solid carriers.

The formulations generally comprise 0.1 to 95% by weight, preferably 0.5to 90% by weight, of one of the compounds I to V or of the mixture ofthe compounds I and II to V. The active ingredients are employed in apurity of 90% to 100%, preferably 95% to 106% (in accordance with NMRspectrum or HPLC).

The compounds I to V or the mixtures or the relevant formulations areused by treating the fungal pests or the plants, seeds, soils, areas,materials or rooms to be protected against them with a fungicidallyactive amount of the mixture or, in the case of separate application, ofthe compounds I and II to V. Application may be effected before or afterinfection with the fungal pests.

USE EXAMPLE Action Against Powdery Mildew Of Wheat (Curative)

Leaves of wheat seedlings cv. “Fr{umlaut over (u)}hgold” in pots wereinoculated with spores of powdery mildew of wheat (Erysiphe graminis f.sp. tritici) and, 24 hours later, sprayed to runoff point with aqueouspreparations of active ingredient which comprised 80% by weight ofactive ingredient and 20% by weight of emulsifier in the dry matter.After the aqueous preparations of active ingredient had dried on, thetest plants were subsequently placed in a greenhouse at from 20 to 22°C. and a relative atmospheric humidity of 75 to 80%. After 7 days, theextent of mildew development was determined.

The visual scores of the percentage of diseased leaf area were convertedinto degrees of efficacy as a percentage of the untreated control. Adegree of efficacy of 0 means the same disease level as in the case ofthe untreated control, a degree of efficacy of 100 is a disease level of0%. The degrees of efficacy to be expected for combinations of activeingredients were determined by Colby's formula (S. R. Colby “Calculatingsynergistic and antagonistic responses of herbicide combinations”, Weeds15, pages 20 to 22 (1967)) and compared with the observed degrees ofefficacy.

The tests were carried out using the following 4 compounds, which wereassigned the symbols (A), (B), (C) and (D) for reasons of simplicity:

A) Untreated control: disease level 44%

TABLE A.1 Degree of efficacy of the individual active ingredientsConcentration of active ingredient Degree of efficacy [% Active in thespray of the untreated ingredient mixture [ppm] control] (A) 16 53 4 5(B) 16 5 (C) 1 64 0.25 0

TABLE A.2 Degree of efficacy of the mixture Mixture of active Observeddegree Expected degree ingredients of efficacy of efficacy 16 ppm (A) +1 ppm (C); 100 83 Mixing ratio 16:1 4 ppm (A) + 0.25 ppm (C); 53 5Mixing ratio 16:1 16 ppm (B) + 1 ppm (C); 98 66 Mixing ratio 16:1

Test result: The observed degree of efficacy in all mixing ratios ishigher than calculated in advance using Colby's formula.

B) Untreated control: disease level 99%

The test was carried out as described for A).

TABLE B.1 Degree of efficacy of the individual active ingredientsConcentration of active ingredient Degree of efficacy [% Active in thespray of the untreated ingredient mixture [ppm] control] (A) 4 0 (B) 4 0(D) 16 39

TABLE B.2 Degree of efficacy of the mixture Mixture of active Observeddegree Expected degree ingredients of efficacy of efficacy 16 ppm (A) +4 ppm (D); 90 39 Mixing ratio 4:1 16 ppm (B) + 4 ppm (D); 95 39 Mixingratio 4:1

Test result: The observed degree of efficacy in all mixing ratios ishigher than calculated in advance using Colby's formula.

We claim:
 1. A fungicidal composition comprising a) a compound of theformula I

 or an N-oxide or salt thereof, wherein R¹, R², R³ and R⁴ are hydrogen,hydroxyl, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio or C₁-C₄-haloalkylthio; R⁵, R⁶ and R⁷are hydrogen, hydroxyl, cyano, nitro, halogen, C₁-C₇-alkyl,C₁-C₇-haloalkyl, C₁-C₇-alkoxy, C₁-C₇-haloalkoxy, C₁-C₇-alkylthio,C₁-C₇-haloalkylthio, C₁-C₇-hydroxyalkyl, C₂-C₄-acyl, aryl or aryloxy, itbeing possible for the radicals with aryl to carry one to three of thefollowing groups: cyano, nitro, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio and C₁-C₄-haloalkylthio,and e) a compound of the formula V

 wherein R¹⁰ is fluorine or chlorine; R¹¹ is trifluoromethyl orchlorine, or R¹⁰ and R¹¹ together are a group —OCF₂O—, in asynergistically effective amount.
 2. The composition defined in claim 1,wherein R¹, R², R³ and R⁴ are hydrogen or halogen, and R⁵, R⁶ and R⁷ arehydrogen or halogen.
 3. The composition defined in claim 1, wherein atleast one of R¹ to R⁴ is halogen.
 4. The composition defined in claim 1,wherein R¹, R², R³ and R⁴ denote hydrogen, fluoro, chloro or bromo. 5.The composition defined in claim 1, wherein R⁵ is halogen, R⁶ ishydrogen or halogen and R⁷ is hydrogen.
 6. The composition defined inclaim 1, wherein R⁵, R⁶ and R⁷ denote hydrogen, fluoro, chloro or bromo.7. The composition defined in claim 4, wherein at least one of R¹ to R⁴is fluoro, chloro or bromo.
 8. The composition defined in claim 6,wherein R⁵ is fluoro, chloro or bromo, R⁶ is hydrogen, fluoro, chloro orbromo and R⁷ is hydrogen.
 9. The composition defined in claim 1, whereinthe weight ratio of the compound I to the compound V is from 10:1 to0.1:1.
 10. A method of controlling fungal pests, which comprisestreating the fungal pests, their environment or the plants, seeds,soils, surfaces, materials or rooms to be protected against said fungiwith a synergistically effective amount of a compound of the formula Ias defined in claim 7 and a compound of the formula V as defined inclaim
 1. 11. The method of claim 10, wherein R¹, R², R³ and R⁴ arehydrogen or halogen, and R⁵, R⁶ and R⁷ are hydrogen or halogen.
 12. Themethod defined in claim 10, wherein at least one of R¹ to R⁴ is halogen.13. The method of claim 10, wherein R¹, R², R³ and R⁴ denote hydrogen,fluoro, chloro or bromo.
 14. The method of claim 10, wherein R⁵ ishalogen, R⁶ is hydrogen or halogen and R⁷ is hydrogen.
 15. The method ofclaim 10, wherein R⁵, R⁶ and R⁷ denote hydrogen, fluoro, chloro orbromo.
 16. The method of claim 13, wherein at least one of R¹ to R⁴ isfluoro, chloro or bromo.
 17. The method of claim 15, wherein R⁵ isfluoro, chloro or bromo, R⁶ is hydrogen, fluoro, chloro or bromo and R⁷is hydrogen.
 18. The method of claim 10, wherein the compound I and thecompound V are applied jointly or separately, or in succession.
 19. Themethod of claim 10, wherein from 0.01 to 0.5 kg/ha of the compound I areapplied.
 20. The method of claim 10, wherein from 0.1 to 1 kg/ha of thecompound V are applied.